Most notable for being Seattle’s weirder—and arguably cooler—vegan sibling, Portland is the ultimate (and tax-free!) shopping destination for folks wanting to channel their inner oddness during this year’s gift-giving season. To take in all the quirky gift shops and toys, handcrafted jewelry with cult followings, and specially made goods available exclusively in Portland, make this trip an overnighter (or an all-weekender).

Portland’s public transportation system undeniably beats Seattle’s, so you can leave your car behind and take Amtrak instead. To spare yourself getting lost in the city, make sure to find out about Portland’s TriMet system, which integrates the city’s buses, MAX Light Rail, and streetcars. You’ll also want to study the map of Portland on your ride down, as it’s separated into four quadrants.

Starting from the Alphabet District in Northwest Portland, head to betsy & iya (2403 N.W. Thurman St., 503-227-5482) to find miraculously affordable handcrafted jewelry, plus clothing, bags, accessories, and more. Each piece is perfectly balanced with thoughtful asymmetry for a boho-chic feel. You can mosey on through to the back of the store to find their onsite studio and see where all the metal magic happens.

In the Southwest, visit Canoe (1136 S.W. Alder St., 503-889-8545), a retail shop specializing in timeless and functional objects for everyday use, such as Eena’s specialty craft canvas bags and Flint & Lars pet toys. This is the perfect spot to find something for the sophisticated and perhaps high-maintenance individual on your list.

The newly developed Union Way Shopping Arcade (1022 W. Burnside St.), which connects downtown Portland’s West End with the Pearl District, is a long, intimate corridor you could mistake for a European-style apartment building. Stop by Quin to find goodies for stocking-stuffers: The candy shop features rich caramels, handmade lollipops, and other classics made with top-notch ingredients. For the burly man-friend on your list, there are two perfect arcade shops to hit before heading home: Danner, Portland’s American-made leather boot company, and Will Leather Goods, a lifestyle brand offering high-end, buttery-smooth leather goods.

If the timing of your trip is right, check out some of the city’s most popular holiday attractions, including the 2014 Holiday Ale Festival (Dec. 3–7, holidayale.com) held at Pioneer Courthouse Square (701 S.W. Sixth Ave.), promoted as the “premier winter beer-tasting venue on the West Coast,” with more than 50 specially brewed winter ales to keep you toasty (and cheerful) for the holidays. And if you’re into crafts or know someone on your gift list who is, make sure to attend the Super Colossal Holiday Sale From Crafty Wonderland (Dec. 13–14, crafty
wonderland.com) at the Oregon Convention Center (777 N.E. Martin Luther King Jr Blvd,, 503-235-7575). It’s a bonanza of more than 250 local vendors selling handmade goods and crafty gifts you can get only in Portland. E